The magazine, which originated in Hyde Park, has been trapped in a long, slow decline for years, though “slow” and “decline” are relative—from seven million at its peak in the 1970s to 1.5 million at the end of the century is a substantial decline, but it’s hardly alone in its weight class. More interestingly is that it recently fell behind Maxim after a massive cut in its subscription base. So the move to Los Angeles is entirely unsurprising. TOC was reporting hints of it earlier this year, and the magazine has been outsourcing and shrinking for longer than that.

Lots of reasons have been given for the magazine’s decline: competition from both softer- and harder-core competition like Maxim and Penthouse; the increasing availability of pornography, from video to VHS to the Internet; the rise of feminism driving soft-core porn from the coffee table and under the mattress; the expansion of the porn industry into hundreds of niches fulfillling every possible taste and fetish; and so forth. But I think there’s something else at work, that has to do with the entropy of all successful artists (yes, I know it’s Playboy, but bear with me for a minute.)

A 1956 memo to Playboy photographers listed Hefner’s criteria for the centerfolds. The model must be in a natural setting engaged in some activity “like reading, writing, mixing a drink.” She should have a “healthy, intelligent, American look—a young lady that looks like she might be a very efficient secretary or an undergrad at Vassar.” Many centerfolds feature the implied presence of a man: a flash of trouser leg in the corner, a pipe left on a table. These props transform the pinups into seduction scenarios. Their premise is simple: by identifying with the absent man, a viewer can enter the scene.

Thanks to the archival work of University of Chicago librarian and Playboy superfan Peggy Wilkins, you can get a sense of this from her complete archive of Playmates. For instance: ignore the naked women and look at their “natural setting.” (Obviously, all of this is NSFW). In 1956, when Hefner wrote his memo, their surroundings are nice, but comparatively modest. September Playmate Elsa Sorensen stands in a mod but spare bedroom, holding roses. Fast forward 40 years, when I was coming of age. January Playmate Victoria Alynette Fuller is in what looks like a ballroom decorated for a French Revival-themed prom thrown by Donald Trump. It doesn’t look like a seduction scenario; it looks like a Caligula remake.

Or take a quick tour through 1966. One big roaring fire, a lot of modest bedrooms. 2006? A naked woman washing a pristine vintage Mustang; another standing in front of a Lichtenstein.

Set aside Hef’s sexist condescension (“a very efficient secretary"), and his goal was clear: to present something the upper-middle-class bachelor could aspire to (putting it, um, politely), or could realistically think he could aspire to. By the time Hefner needed to get young men of my age to replace his aging audience, Playboy centerfolds were ludicrous camp.

And that’s even setting aside the models themselves. Young describes their evolution:

Flesh and blood women turn to images; the “girl next door” becomes distinctly mediated. The bunnies were always mediated, of course, but something about the earlier photographs made you forget the medium and feel as though you were staring straight into the eyes of a luscious partner. Enthusiastic photoshopping has aided the transformation. Gone are the freckles and downy arm hairs of the predecessors. Breasts are surgically standardized; gym routines and spray tans produce identically toned and tinted bodies. Girls of all ethnicities blend together into one latte-colored woman, and the result looks computer-generated.

The first time I was exposed to Playboy, I just thought it was weird. Not out of any particular aversion to nude women, but because the whole package was just on the wrong side of the uncanny valley: kind of synthetic, kind of a put-on, and not particularly sexy.

Don’t just take it from my jaundiced eye. There’s some mathematical basis for the evolution of the Playboy centerfold in increasingly unrealistic directions. Wired charted the measurements of centerfolds over time, and found that their BMI has fallen over time while bust size has remained steady: “a sylphlike 19.4 to an anime-ideal 17.6.” (BMI is a wildly flawed metric, but here it at least gives some indication of the direction of the magazine.)

Hugh Hefner started as a middle-class Chicago kid who mortgaged his furniture to follow his Playboy dream, and in its early days the Playmates look like women an Esquire copywriter might dream about. His vision turned into vast wealth and a lifelong parade of Bunnies, and the heart of the magazine evolved from a daydream into a hallucination. He became the Willy Wonka of sex, with all the eeriness that entails.

The party did not stop for Hefner, of course. If anything, the Los Angeles mansion and the parties there have outshone the Chicago originals. In the years immediately after he moved to L.A. permanently, he seemed determined to bury all memories of his Chicago days under a blizzard of sexual pleasures. Soon enough, a new set of tales, scandals, and legends grew up, and within a few years, it was as if the glory days in Chicago were nothing more than some distant, quaint fantasy. As with the endless string of beauties he had wooed, loved, and eventually drifted apart from, Hefner had left the mansion behind.

Playboy long ago left Chicago, and the departure of the editorial operations were long overdue, following Hef and his vision in the direction of the sunset.